3-(1-Cyclohexenyl)-1-phenyl-1-butyn-3-ol | 152589-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(1-Cyclohexenyl)-1-phenyl-1-butyn-3-ol
• 英文别名: 2-(cyclohexen-1-yl)-4-phenylbut-3-yn-2-ol
• CAS: 152589-43-0
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: FOXBEVFOCQQTGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(1-Cyclohexenyl)-1-phenyl-1-butyn-3-ol 在 三氟化硼乙醚 、 silver(I) acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 20.0~25.0 ℃ 、1.0 MPa 条件下， 反应 5.0h， 生成 trans-3-methyl-1-phenyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-one
  参考文献：
  名称：

  二氧化碳介导的立体定向脱羧纳扎罗夫环化反应制备高度取代的2-环戊烯酮

  摘要：

  通过路易斯酸催化的环状碳酸酯衍生物的脱羧纳扎罗夫环化反应，以高催化效率立体选择性和区域选择性地构建了高度取代的2-环戊烯酮，环状碳酸酯衍生物是通过使炔丙基醇与二氧化碳在银催化剂存在下反应制备的。2-环戊烯酮的立体化学严格受起始材料中烯烃的几何形状控制。该方法适用于各种基板。

  DOI：

  10.1002/anie.201705909
• 作为产物：
  描述：

  苯乙炔 、 乙酰基环已烯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 3-(1-Cyclohexenyl)-1-phenyl-1-butyn-3-ol
  参考文献：
  名称：

  二氧化碳介导的立体定向脱羧纳扎罗夫环化反应制备高度取代的2-环戊烯酮

  摘要：

  通过路易斯酸催化的环状碳酸酯衍生物的脱羧纳扎罗夫环化反应，以高催化效率立体选择性和区域选择性地构建了高度取代的2-环戊烯酮，环状碳酸酯衍生物是通过使炔丙基醇与二氧化碳在银催化剂存在下反应制备的。2-环戊烯酮的立体化学严格受起始材料中烯烃的几何形状控制。该方法适用于各种基板。

  DOI：

  10.1002/anie.201705909

文献信息

• Regiocontrolled synthesis of furans by a mercury(II) catalysed isomerisation of 1-alkynyl-2,3-epoxyalcohols
  作者：Charles M. Marson、Steven Harper、Roger Wrigglesworth

  DOI：10.1039/c39940001879

  日期：——

  2,3,5-Trisubstituted furans are formed by the reaction of 1-alkynyl-2,3-epoxyalcohols with a catalytic amount of mercury(II) prepared from HgO and dilute sulfuric acid.

  2,3,5-三取代呋喃是通过 1-炔基-2,3-环氧醇与催化量的由 HgO 和稀硫酸制备的汞 (II) 反应形成的。
• Pt-Catalyzed Tandem Epoxide Fragmentation/Pentannulation of Propargylic Esters
  作者：Brian G. Pujanauski、B. A. Bhanu Prasad、Richmond Sarpong

  DOI：10.1021/ja061549m

  日期：2006.5.1

  A Pt-catalyzed pentannulation of propargylic esters containing an epoxide moiety has been developed. The present transformation achieves the formation of cyclopentenone products as single diastereomers in good yields. The observed products likely form from pyran intermediates that undergo an oxa-6pi electrocyclic ring opening to a functionalized dienone, followed by ring closure with an accompanying acyl shift.
• Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms
  作者：Charles M. Marson、Andrew J. Walker、Jane Pickering、Adrian D. Hobson、Roger Wrigglesworth、Simon J. Edge

  DOI：10.1021/jo00074a019

  日期：1993.10

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.
• Synthesis of polysubstituted thiophenes by a catalytic cyclisation of functionalised episulfides
  作者：Charles M. Marson、Jonathan Campbell

  DOI：10.1016/s0040-4039(97)01819-4

  日期：1997.11

  Substituted thiophenes are formed by the reaction of 1-alkynyl-2,3-epithioalcohols with a catalytic amount of mercury(II) prepared from HgO and dilute sulfuric acid. (C) 1997 Elsevier Science Ltd.
• Catalytic Isomerization of 1-Alkynyl-2,3-epoxy Alcohols to Substituted Furans:  Succinct Routes to Furanoid Fatty Acids and Difurylmethanes
  作者：Charles M. Marson、Steven Harper

  DOI：10.1021/jo980856a

  日期：1998.12.1

  A versatile procedure for the preparation of synthetically valuable 2,5-disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)-catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic Phi-alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F-5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(alpha-hydroxyalkyl)furans 4.